Alpha-hydroxyimino-alkylquinolinium salts having fungicide action

Abstract

There are disclosed alpha-hydroxyimino-alkylquinolinium salts having fungicidal action and, more particularly, alpha-hydroxyimino-alkylquinolinium salts which are active in vivo against Peronospora, Oiduim, Botrytis, against the Fusicladium which attacks apple trees and the rust of the bean plant.

We claim: 
     
       1. Alpha-hydroxyimino-akylquinolinium salts of the formula ##STR8## wherein: R is H or OH; R 1  is H or alkyl containing 1 to 5 carbon atoms;   R 2  is CN; ##STR9## in which R 3  is alkyl containing 1 to 5 carbon atoms or phenyl; selected from the group consisting of Cl, Br and I.   
     
     
       2. Betaines resulting from the elimination of the acid corresponding to the anion X -  from the compounds of claim 1 in which R is OH and having the formula ##STR10## in which R 1  is H, lower alkyl or halogen; and R 2  is CN or O = CR 3  in which   R 3  is alkyl containing 1 to 5 atoms or phenyl.   
     
     
       3. A compound according to claim 1, characterized in being 8-hydroxyquinolinium-N-(2-hydroxyimino-butan-3-on-yl) chloride or the corresponding betaine. 
     
     
       4. A compound according to claim 1, characterized in being quinolinium-N-(alpha-hydroxyimino-propionitrile) chloride. 
     
     
       5. A compound according to claim 2, characterized in being 8-hydroxyquinolinium-N-(2-hydroxyimino-butan-3-on-yl) betaine. 
     
     
       6. A compound according to claim 1, characterized in being 4-methylquinolinium-N-(2-hydroxyimino-3-on-yl) chloride. 
     
     
       7. A compound according to claim 1, characterized in being 4-methylquinolinium-N-(alpha-hydroxyimino-propionitrile) chloride. 
     
     
       8. A compound according to claim 1, characterized in being 4-methylquinolinium-N-(alpha-hydroxyimino-propiophenyl) chloride. 
     
     
       9. A compound according to claim 1, characterized in being 8-hydroxyquinolinium-N-(alpha-hydroxyimino-propiophenon-yl) chloride. 
     
     
       10. The process for preparing the compounds of claim 1, in which equimolar quantities of a quinoline compound of the formula ##STR11## in which R is H or OH; and R 1  is alkyl containing 1 to 5 carbon atoms, or halogen are reacted in a solvent, at room temperature of under heating and with stirring, with an alpha-chloroalkyl-hydroxyimine of the formula ##STR12## in which R 2  is CN; ##STR13## in which R 3  is alkyl containing 1 to 5 carbon atoms or phenyl.   
     
     
       11. The process of claim 10, in which the solvent is ethanol or tetrahydrofuran, and the reaction is carried out at room temperature or under heating. 
     
     
       12. The process for preparing betaines of claim 2, characterized in that HX is eliminated from N (alpha-hydroxyiminoalkyl) 8-hydroxyquinolinium salts according to the reaction: ##STR14## R 1  being H, alkyl containing 1 to 5 carbons, or a halogen atom and R 2  being CN or ##STR15## in which R 3  is alkyl containing 1 to 5 carbons or phenyl. 
     
     
       13. The method of combatting or preventing fungine infections of plants by Botrytis cinerea, Sphaerotheca fuliginea and Fusicladium dendriticum, which comprises applying to the plants to be protected powders, suspensions or solutions of the compounds of claim 1, in an amount of at least 15 micrograms per sq. cm of foliar surface.